Microbial production of vitamin B12 antimetabolites. IV. Isolation and identification of 4-keto-5-amino-6-hydroxyhexanoic acid.
4-Keto-5-amino-6-hydroxyhexanoic acid was isolated from Bacillus cereus 102804 fermentations and found to inhibit the growth of Gram-positive and Gram-negative bacteria, when grown in a chemically defined medium. The mechanism appeared to be the inhibition of delta-aminolevulinic acid dehydratase. The Ki value of 4-keto-5-amino-6-hydroxyhexanoic acid in an enzyme preparation of Propionibacterium shermanii was 0.72 microM. Similar test conditions with 4-keto-5-aminohexanoic acid resulted in Ki of 12.1 microM. In both cases competitive inhibition was found. The structure of 4-keto-5-amino-6-hydroxyhexanoic acid was determined.
D000614:Aminocaproates; D000963:Antimetabolites / Q000302:isolation & purification*; D001409:Bacillus cereus / Q000378:metabolism*; D001419:Bacteria / Q000254:growth & development; D002208:Caproates / Q000138:chemical synthesis / Q000302:isolation & purification*; D055598:Chemical Phenomena; D002621:Chemistry; D005285:Fermentation; D007700:Kinetics; D000623:Porphobilinogen Synthase / Q000037:antagonists & inhibitors; D014805:Vitamin B 12 / Q000378:metabolism
D000614:Aminocaproates; D000963:Antimetabolites; D002208:Caproates; C031350:4-keto-5-amino-6-hydroxyhexanoic acid; D000623:Porphobilinogen Synthase; D014805:Vitamin B 12